Following the blue blazes, the trail begins to descend for 1/3 of a mile to the intersection of Paradise Lane and the Appalachian Trail, easily identified by its white blazes. Turn left onto the Appalachian Trail (don't turn right on the unmarked trail which leads to private property) and continue following the white blazes to the most challenging part of this hike. Here, you will have to traverse steep slopes of ledge that go straight up for almost 1/4 of a mile.
As you begin to climb look for natural hand and toe holds to help you scramble up Bear Mountain's steep rock face for the final 1/3 of a mile (500 vertical feet). As you ascend the face of Bear Mountain, look to the north, over your shoulder, for expansive views of Connecticut's beautiful Litchfield Hills and beyond.